Catalytic Asymmetric Mannich-Type Reaction of α-Haloacetonitriles.

An asymmetric Mannich-type addition of aldimines and haloacetonitriles is reported here, yielding halogenated aminonitriles with excellent stereoselectivity, facilitated by a pincer Ni(II) complex as a catalyst. Haloacetonitriles are recognized as reactive electrophiles, and the possibility of their use as a pronucleophile has been almost neglected for many years. The resulting adduct can be readily converted into various valuable derivatives, including chiral aziridines, starting from chlorinated compounds.